(Z)-1-chloro-2-3,3,3-tetrafluoropropene (HCFO-1224yd (Z)) and (Z)-1,2-dichloro-3,3,3-trifluoropropene (HCFO-1223xd (Z)) are useful as raw materials of, for example, a foaming agent of hard polyurethane foam, a solvent, a cleaning agent, a refrigerant, a working fluid, a propellant, and fluorocarbon resin.
In this specification, an abbreviation of a compound being halogenated hydrocarbon is given in a parenthesis after the name of the compound, and the abbreviation is used instead of the name of the compound as required. Further, as for a compound having a double bond in its molecule and existing as an E-isomer and a Z-isomer, its E-isomer and Z-isomer are respectively represented by (E) and (Z) each added at the end of the abbreviation of the compound. An abbreviation of a compound name without the notation of (E) or (Z) at the end represents an E-isomer and/or a Z-isomer.
As a method of producing HCFO-1224yd, US 2012/0215037 A1 describes a method to obtain HCFO-1224yd by bringing vapor-phase 1,2-dichloro-2-3-3-3-tetrafluoropropane (HCFC-234ba) into contact with a potassium chloride catalyst carried by carbon to cause the HCFC-234ba to undergo a dehydrochlorination reaction. Further, WO 2009/035130 A1 describes a method to obtain HCFO-1224yd by causing 1-chloro-2,2,3,3,3-pentafluoropropane (HCFC-235cb) to undergo a dehydrofluorination reaction by using a base such as potassium hydroxide. WO 2009/035130 A1 also describes to obtain 2,3,3,3-tetrafluoropropene (HFO-1234yf) by hydrogen-reducing the obtained HCFO-1224yd in the presence of a catalyst.
Further, WO 2011/162338 A1 describes a method to obtain HFO-1234yf by causing a raw material compound gas containing at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO-1214ya) and HCFO-1224yf to react with hydrogen in the presence of a palladium catalyst carried by carbon. WO 2011/162338 A1 also describes that as a result of the hydrogen reduction of CFO-1214ya, HCFO-1224yd is produced.
In these methods, however, HCFO-1224yd is usually obtained as a mixture of an E-isomer and a Z-isomer, which is inconvenient for the use of only one of the geometric isomers. This has given rise to a demand for a method to selectively produce one of HCFO-1224yd (E) and HCFO-1224yd (Z) by an industrially advantageous and efficient method.
There is also a demand for an industrially advantageous and efficient method that selectively produces one of an E-isomer and a Z-isomer of HCFO-1223xd similarly to the above.